4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester
• CAS No.: 691391-08-9
• Molecular Formula: C₂₆H₃₇BrO₄Si
• Molecular Weight: 521.567

Synonyms:4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester

Chemical Property of 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester

Chemical Property:

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Technology Process of 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester

There total 3 articles about 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

4-chlorobenzoyl chloride (586-75-4) + (1S,3R,6S,7R,8S)-1-Triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-ol (691391-18-1) → 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester (691391-08-9)

Guidance literature:

With pyridine; dmap; at 65 ℃;

DOI:10.1021/ja049323b

Reference yield:

2-(triisopropylsiloxy)-1,3-butadiene (139278-54-9) → 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester (691391-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1: oxazaborolidinium⁽¹⁺⁾*Tf₂N^(1-) / CH₂Cl₂ / 6 h / -78 °C

2: 68 percent / aq. CeCl₃; NaBH₄ / methanol / 0.17 h / 0 °C

3: 85 percent / BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 °C

4: 87 percent / pyridine; 4-(dimethylamino)pyridine / 65 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; oxazaborolidinium⁽¹⁺⁾*Tf₂N^(1-); boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; dichloromethane; 1: Diels-Alder reaction / 2: Luche reduction;

DOI:10.1021/ja049323b

Reference yield:

(4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione (691390-89-3) → 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester (691391-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / aq. CeCl₃; NaBH₄ / methanol / 0.17 h / 0 °C

2: 85 percent / BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 °C

3: 87 percent / pyridine; 4-(dimethylamino)pyridine / 65 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; 1: Luche reduction;

DOI:10.1021/ja049323b

upstream raw materials:

4-chlorobenzoyl chloride

(1S,3R,6S,7R,8S)-1-Triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-ol

2-(triisopropylsiloxy)-1,3-butadiene

(4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione

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